Alkanes from Achillea Asplenifolia Vent . Udc 547

Slobodan Milosavljevi

Alkanes from Achillea Asplenifolia Vent . Udc 547

Slobodan Milosavljevi

2001

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The hydrocarbon fraction of Achillea asplenifolia Vent. has been analyzed by capillary gas chromatography (GC) and GCmass spectrometry (GC-MS). It was found to consist of the usual odd-carbon number dominant distribution of n-alkane homologues (C21-C33). The main compound was nonacosane (C29, 25.5%) and the carbon preference index (CPI) was low (6.87).

UNIVERSITY OF NIŠ The scientific journal FACTA UNIVERSITATIS Series: Physics, Chemistry and Technology Vol. 2, No 1, 1999 pp. 27 - 30 Editor of series: Momčilo Pejović, e-mail: [email protected] Address: Univerzitetski trg 2, 18000 Niš, YU Tel: +381 18 547-095, Fax: +381 18 547-950 ALKANES FROM ACHILLEA ASPLENIFOLIA VENT. UDC 547.21+547.473 Nebojša Simić1, Radosav Palić1, Slobodan Milosavljević2, Vlatka Vajs2, Dejan Djoković2, Novica Randjelović3 1 Department of Chemistry, Faculty of Mathematics and Natural Sciences, University of Niš, PO Box 91, 18000 Niš, Yugoslavia, E-mail: [email protected] 2 Faculty of Chemistry, University of Belgrade, Studentski trg 16, 11001 Belgrade, Yugoslavia 3 Faculty of Technology, University of Niš, 16000 Leskovac, Yugoslavia Abstract. The hydrocarbon fraction of Achillea asplenifolia Vent. has been analyzed by capillary gas chromatography (GC) and GC- mass spectrometry (GC-MS). It was found to consist of the usual odd-carbon number dominant distribution of n-alkane homologues (C21-C33). The main compound was nonacosane (C29, 25.5%) and the carbon preference index (CPI) was low (6.87). Key words: Achillea asplenifolia, n-alkanes, n-nonacosane INTRODUCTION Achillea asplenifolia Vent. (2n = 18, Section Millefolium, group A. millefolium) is a species with restricted spreading from Czech and Slovak Republic southwards to Central Yugoslavia and South Romania. Stem is 40-100 cm high, with pink to purplish-red, rarely white flowers. It usually grows on wet lowland meadows [1]. A. asplenifolia was subject of a few chemical studies concerning essential oil [2] and its antibacterial activity [3]. Proazulenes were also investigated by Kastner et al. [4]. Protecting coats, so called »waxes«, on the leaves of ground plants have an almost universal occurance. Their main functions are to protect plants from physical damage and, esspecially, from the loss of water. The main components of the waxes are n-alkanes with odd and even numbers of C-atoms (C21-C37, C20-C30), branched alkanes (C27-C33), higher alcohols and acids (usually in the form of esters), aldehydes (as polimers) and ketones. Odd-carbon alkanes are usually prevailing in the alkane fraction [5]. Received December 8, 1999 28 N. SIMIĆ, R. PALIĆ, S. MILOSAVLJEVIĆ, V. VAJS, D. DJOKOVIĆ, N. RANDJELOVIĆ There are opinions that carbon preference index (CPI) and average chain length (ACL) could be used as a chemotaxonomic marker at a genus level [6, 7, 8]. Alkanes, as possible chemotaxonomic markers, were investigated in this study. The aim of the paper is to provide the first information about alkane composition of this plant species. EXPERIMENTAL Plant material. Plant material was collected in the blooming stage of vegetation (August 21, 1998), on the locality Selevenj medow near Horgoš, Yugoslavia. A voucher specimen is deposited in the private herbarium of Dr Novica Randjelović (Herbarium Moesiacum Doljevac), who also identified the plant. After separation from underground parts, aerial parts of the plant were air-dried for ten days at room temperature. Extraction and isolation. The dried plant material was extracted using the procedure reported earlier [6]. The extraction of 100 g of the plant material gave 1.97 g of residue. Fractionation on CC [6] and precipitation of the alkane fraction gave 78 mg of alkanes. Identification procedure. The alkane fraction was analyzed on an analytical gas chromatography (GC) and a gas chromatography-mass spectrometry (GC-MS). The constituents were identified by coinjection of authentic hydrocarbon standards and by comparison of their retention indices along with mass spectra to those from the MS library [9]. The percentage of the components (Table I) was computed from GC (FID) peak areas without using correction factors. GC. The analysis was carried out on a gas chromatograph Varian model 3400, fitted with a FID and a 60 m x 0.25 mm fused silica capillary column, with a 0.3 µm film thickness of DB-5. Carrier gas was He (2 mLmin-1.). The operating conditions were: temperature program 50°C - 285°C at 15°Cmin-1 and an injector and detector temperature of 300°C. GC-MS. GC-MS analyses were performed on a Finigan Mat, model 8230, equipped with a fused silica 30 m x 0.25 mm, PTE-5 capillary column, with a film thickness 0.25 µm; carrier gas was H2 (2.5 mLmin-1.) with the same temperature program as for the analytical GC. Ionization potential was 70eV with an ion source temperature of 180°C. RESULTS AND DISCUSSION The content and composition of alkanes of A. asplenifolia are shown in Table 1. As it can be seen, odd-carbon number alkanes are dominant, maximizing at C29, what was also remarked for A. lingulata, A. nobilis, A. crithmifolia [6] and A. serbica [10]. However, a high content of nonacosane was also found in Satureja genus [7, 8], what diminishes its importance as a possible chemotaxonomic marker for the genus Achillea. Average chain length (ACL) value was lower than those in the other Achillea species [6, 10]. CPI had the lowest value of those reported earlier for the above-mentioned Achillea species [6, 10]. A. lingulata, A. nobilis, A. crithmifolia, A. serbica and A. asplenifolia belong to different sections of the genus Achillea [1]. Therefore, the differences between them in CPI and ACL are rather expected. However, although insufficient for a general conclusion, the obtained results suggest that it is very likely that 29 Alkanes from Achillea Asplenifolia Vent. CPI similarities in the genus Achillea L. do not appear at the genus level. Table 1. Composition of the n-alkane fraction of Achillea asplenifolia Alkanes Heneicosane Docosane Tricosane Tetracosane Pentacosane Hexacosane Heptacosane Octacosane Nonacosane Triacontane Hentriacontane Dotriacontane Tritriacontane CPI ACL Carbon No. 21 22 23 24 25 26 27 28 29 30 31 32 33 Total: 6.87 20.18 % 1.3 0.5 2.4 1.3 7.1 1.5 12.1 2.4 25.5 2.5 13.1 0.9 1.0 71.6 Acknowledgements. The authors thank the Ministry of Science & Technology of Republic of Serbia for financial support of this study. REFERENCES 1. B. K. Richardson, Achillea L. in Flora Europaea (T. G. Tutin, V. H. Heywood, N. A. Burges, D. M. Moore, D. H. Valentine, S. M. Walters and D. A. Webb, eds), Cambridge University Press, Cambridge, 4 (1976)159 2. É. Héthelyi, B. Dános and P. Tétényi, Phytochemical Studies on the Essential Oils of Species Belonging to the Achillea Genus by Gas Chromatography/Mass Spectrometry, Biomed. Environ. Mass Spec., 18, 629-636 (1989) 3. N. Simić, G. Stojanović, R. Palić, T. Nasković, S. Anđelković, M. Dimić, R. Danilović, Mikrobiološka aktivnost etarskog ulja Achillea asplenifolia Vent., 6. Simpozijum o flori Jugoistočne Srbije i susednih područja, (accepted in March 1999) Sokobanja (2000) 4. U. Kastner, J. Jurenitsch, S. Glasl, A. Baumann, W. Robien, W. Kubelka, Proazulenes from Achillea asplenifolia, Phytochem., 31 (12) 4361-4362 (1992) 5. E. L. Wynder, D. Hoffmann, Tobacco and Tobacco Smoke, 365, Academic Press, New York & London (1967) 6. R. Palić, T. Eglinton, B. C. Benitez-Nelson, G. Eglinton, J. Veličković and G. Stojanović, Alkanes from Plants of the Genus Achillea, J. Serb. Chem. Soc. 64, 443-446 (1999) 7. R. Palić, D. Savić, N. Simić and S. Andjelković, The Alkanes from Some Plants of Satureja Genus, Facta Universitatis 1 (1), 91-94 (1994) 8. D. Kitić, R. Palić, N. Ristić, G. Stojanović, The fatty acids and alkanes of Satureja adamovicii Šilić and Satureja fukarekii Šilić, J. Serb. Soc., 64 (5-6), 389 (1999) 9. NIST 92 Mass Spectral Library, National Institute of Standards & Technology, Gaithersburg, MD (1992) 10. N. Simić, S. Andjelković, R. Palić, S. Milosavljević, V. Vajs, D. Djoković and N. Randjelović, (sent for publishing in J. Serb. Chem. Soc. in November, 1999) 30 N. SIMIĆ, R. PALIĆ, S. MILOSAVLJEVIĆ, V. VAJS, D. DJOKOVIĆ, N. RANDJELOVIĆ ALKANI IZ ACHILLEA ASPLENIFOLIA VENT. Nebojša Simić, Radosav Palić, Slobodan Milosavljević, Vlatka Vajs, Dejan Djoković, Novica Randjelović U ovom radu ispitivana je ugljovodonična frakcija ekstrakta Achillea asplenifolia Vent. gasnom hromatografijom (GC) i GC- masenom spektrometrijom (GC-MS). Rezultati su pokazali uobičajenu dominantnu raspodelu n-alkana sa neparnim brojem C-atoma (C21-C33). Nonakozan (C29) je najzastupljenije jedinjenje (25,5%). Preferencijalni ugljenični indeks (odnos alkana sa neparnim i parnim brojem C-atoma, CPI) ima malu vrednost (6,87). Ključne reči: Achillea asplenifolia, n-alkani, n-nonakozan

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